Karen C. Brown, Kathryn L. Poindexter, Paul D. Dossa, paul_dossa@hmc.edu, and David A. Vosburg, david_vosburg@hmc.edu. Department of Chemistry, Harvey Mudd College, 301 Platt Blvd, Claremont, CA 91711 |
Davanone, the major component of the essential oil of Artemisia pallens, possesses both spasmolytic and fungolytic activity. Our proposed synthesis should be the shortest yet, as well as being enantioselective and offering a route to related natural products. The key steps are a thiazolium-catalyzed asymmetric epoxide opening and a biomimetic cyclization to form a trisubstituted tetrahydrofuran ring. Our synthetic work towards (+)-davanone, including these pivotal steps, will be presented. |
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Materials, Devices and Switches, Metal-Mediated Reactions, Asymmetric Reactions, Total Synthesis, Biologically-Related Molecules and Processes
7:00 PM-9:00 PM, Wednesday, April 9, 2008 Morial Convention Center -- La Louisiane, Blrm. C, Poster
Sci-Mix
8:00 PM-10:00 PM, Monday, April 7, 2008 Morial Convention Center -- Hall A, Sci-Mix
Division of Organic Chemistry
The 235th ACS National Meeting, New Orleans, LA, April 6-10, 2008
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